What To Wear On A First Date For Men By Tapered Menswear

What To Wear On A First Date For Men

You've picked the day and the time is set, waiting like a promise. You feel butterflies matching your heartbeat – it's your first date. This day is special, filled with hope for something great.

But choosing what to wear on a first date can be daunting for many men. Deciding on the perfect outfit as the clock ticks away for Date Night. Your first impression is instant so making the right outfit choice is crucial.

So what should men wear on a first date? For a first date, men should aim for a smart-casual look that feels comfortable yet polished, such as a well-fitted button-down shirt paired with dark jeans or chinos. Depending on the venue, adding a blazer or a stylish sweater can elevate the outfit, and finishing with clean, appropriate footwear like loafers or neat sneakers ensures a good impression.

I will explore men's fashion for first dates in this blog, how to catch the eye immediately. Plus, the best fitting clothing for a first date right here at Tapered Menswear.

best fitting clothing for men to wear on a first date

The Power Of A Good First Impression

Choosing what to wear on a first date can shape the whole experience. A first impression is made in seconds. Your clothes are a way to communicate, not just outfits.

Positive feelings, like a big smile, make a huge difference in how people see your personality and appeal. So, dressing well for a first date is more than clothes. Your smile and how you act are just as important.

Your outfit can make you look good and feel good. It can show off things like broad shoulders or a fit body. It also tells people you care about how you look and pay attention to details.

The Psychology Behind First Impressions

Studies show nonverbal communication is key. A 2009 study found body language speaks louder than fancy clothes.

And in 2021, research showed a happy face may make you appear more trustworthy. Picture this: you walk in, well-dressed, with a real smile and a firm handshake.

You’ve shown you’re reliable and friendly without saying a word.

The Impact Of Your Apparel

What you wear can make your date see you as someone they can trust and have a connection with. Choose clothes that make you look like you care about your appearance.

best fitting denim shirts for men to wear on a first date

What Not To Wear On A First Date

Getting ready for a first date is not just about choosing the right outfit. It's also knowing what to avoid wearing on a first date. First impressions are quick and powerful.

Your choice of clothes matters a lot. For men, some style mistakes might ruin your chance before you even speak.

Athletic wear is too casual for a first date. It's key to avoid men's fashion faux pas like joggers and trainers. They might look like you didn't try hard enough. Instead, choose clothes that show respect and thought for the occasion and your date.

The British highlight dating style tips for men with a top 10 list of items to avoid. This includes matching tracksuits and Crocs. While 24% of men think their clothes don't matter, 41% of women disagree.

Fashion mistakes are more unforgivable to women than men. This shows the need for thought-out and appealing men's date night styles.

Wearing clothes that are too tight or too loose is not good either. You want to be comfortable and relaxed.

But, your clothes must also look good. Avoid shirts that don’t fit right, trousers that are baggy, or clothes that are dirty. Choose clothes that fit well and make you look neat. 

best fitting olive shirt for men to wear on a first date

The shoes you pick say a lot about you. Shoes that don't fit the occasion can spoil a good look. Sandals are often a bad choice for a first date, especially for men over 55. This is because of what people expect.

Don't try a new style for the first time on your date. Stick to reliable classics like a white shirt and smart jeans. They are sophisticated but relaxed. Wearing clothes that reflect your true style helps you feel confident.

This is key for a good first impression.

What Guys Should Wear On A First Date?

Getting ready for a first date can make anyone anxious. The clothes you pick are very important.

A study from Princeton found we judge others in just 1/10th of a second. So, what you wear on a date really matters for first impressions.

When picking an outfit, aim for something stylish yet comfy. Choosing a sharp button-down shirt could work in your favour. Pair it with dark jeans or chinos for a look that's friendly and a bit posh.

Don't forget about shoes. Boots were the top choice among women, but white sneakers and dress shoes are a solid choice too. 

Polo shirts and T-shirts are easy picks for more casual dates or if a dress shirt is too formal. Just make sure the fit is right!

best fitting t-shirts for men to wear on a first date

Choosing the right colours is vital too. White and black are easy picks for dates. Yet, it's important to choose colours that suit your skin and set the right mood.

Dress Shirt Versus T-Shirt: A Strategic Choice 

When deciding between a dress shirt and a t-shirt for a first date, it's essential to consider the impression you want to make and the context of the date. 

Going for a dress shirt can certainly boost your appearance and show that you’ve put extra effort into your look. This might well be interpreted as a sign of respect and seriousness about the date.

Shop Better Fitting Dress Shirts

A dress shirt strikes a balance between formal and casual, making it versatile enough for most dating scenarios.

On the other hand, wearing a t-shirt might seem too casual, especially if the other person opts for a more dressed-up look. This mismatch can create a sense of imbalance and might suggest a lack of effort or consideration for the occasion. 

However, it’s also important to consider comfort and authenticity. If the setting is genuinely informal, or if wearing a dress shirt feels out of character, a clean, well-fitted t-shirt can be appropriate.

best fitting white t-shirt for men to wear on a first date

Ultimately, the choice should reflect not only the occasion but also your personality, ensuring you feel confident and genuine on your first date.

Ultimately whichever you choose just make sure they fit correctly. No unwanted bagginess around the arms or torso.

Check out our Tapered Fit T-Shirts here.

Colour And Print: Express Your Personality Tactfully

Choosing the right colours and prints speaks volumes. Neutral colours like black, navy, or gray are safe bets for first dates as they convey a range of positive attributes: sophistication, stability, and a grounding presence.

These colours are versatile and typically well-received, making them suitable for a variety of venues and they pair easily with other garments and accessories.

On the other hand, opting for brighter colours such as red or blue can be strategic. Red is known for its association with passion and confidence, making it a strong choice if you want to leave a memorable impression.

Blue, particularly in softer shades, is universally flattering and suggests reliability and calmness, traits that are appealing in a potential partner.

best fitting turquoise t-shirt for men to wear on a first date


The key is to choose a colour that not only suits the occasion but also enhances your natural features—skin tone, hair colour, and eye colour.

Lighter skin tones may look best with darker shades, which provide a striking contrast, while deeper skin tones can stand out with both rich and bright colours.

Prints are a silent way to show off your personality on a date. The right print can say a lot about you without words.

From floral prints showing openness to stripes and plaids showing reliability, your style gets noticed.

Changing from casual to a sharper look, like dark jeans and leather shoes, highlights the power of prints.

The Rule Of Thirds: Balancing Your Outfit Proportions

In fashion, the rule of thirds provides a framework for assembling an outfit that balances visual interest with cohesion, making it a particularly useful guideline for dressing for any occasion, including first dates.

Here’s how to apply this principle to create a stylish and thoughtful outfit:

  1. Main Element: This component forms the bulk of your outfit, comprising about two-thirds of your visible attire. This might include your primary clothing items such as trousers and a shirt. These pieces should generally be more understated or in neutral tones, offering a solid foundation for your ensemble.

  2. Secondary Element: This part of your outfit should complement the main element, adding depth and layers to your look. It could be a blazer, sweater, or a different style of top that contrasts with the base layer in texture or style, rather than colour alone. This secondary element, taking up roughly one-third of your outfit, enhances the overall aesthetic without overpowering the main pieces.

  3. Accent Details: Finally, the smallest portion of your outfit should focus on accessories and finer details, such as a statement watch, distinctive shoes, unique jewelry, or a stylish bag. These details might only make up a small fraction of your look but they are pivotal in expressing individuality and flair. On a first date, these accents can communicate your personal style and attention to detail, contributing to a memorable impression.

Who knew first date dressing would be this stressful ay! Applying the rule of thirds in this way helps to create an outfit that is visually balanced and stylish, ensuring that each element from clothing to accessories works harmoniously together.

best fitting polo shirt for men to wear on a first date

This strategic approach to fashion is particularly effective in a first date scenario, where making a good first impression is key.

Is It Okay To Wear Jeans On A First Date?

Wearing jeans on a first date is absolutely okay, provided that they fit well and are appropriate for the venue.

The key to pulling off jeans on a first date—or any date, really—is ensuring they have a perfect fit. Jeans that are well-tailored to your body shape can look polished and intentional.

Ideally, they should hug your waist without needing a belt to stay in place, and the hem should hit just right, neither dragging on the ground nor floating above the ankle, unless deliberately styled as cropped.

best fitting jeans for men to wear on a first date

The fit around the thighs and seat should be snug but not tight, allowing room for movement without looking baggy.

When jeans fit this way, they elevate a casual material to something more sophisticated and stylish.

Thus, with the right fit, jeans can be a smart choice for a first date, so long as they fit correctly!


Preparing For The Seasons: Adaptable Date Outfits 

In the cold months, semi-formal wear is the best choice. It allows for versatility and personal style. A smart knitwear item, like a fine gauge knit, can replace a shirt. This adds a modern flair to your look.

Earthy coloured suits are trendy, giving a fresh take on classic style. The preference for slim cuts has changed to wider cuts. These celebrate natural body shape and still look tailored.

What To Wear On A First Date Men Summer

In summer, choose outfits with breathable fabrics like linen. Light colours help stay cool while looking smart. Trainers can now be stylishly worn with an unstructured cotton suit and T-shirt. This gives a casual yet fashionable summer look.

Forget outdated rules like 'no brown in town'. Modern dating is about showing your true self with comfy fashion.

For shoes, versatile Derby shoes or Chelsea boots work well. They suit both jeans and more tailored outfits, preparing you for any date activity.

Casual First Date Outfit Ideas

Getting the right casual first date outfit ideas means finding that sweet spot. Here at Tapered Menswear find some inspiration below on some of our top picks:

best fitting black t-shirt for men to wear on a first date
Black Tapered Fit T-Shirt with trousers and sneakers.
Tapered Menswear's navy chinos, designed in an athletic fit with added stretch for everyday wear. 
 best fitting denim shirt to wear on a first date
best fitting white polo for men to wear on a first date

Tapered Fit Polo Shirt with Black Tapered Fit Jeans


Best Fitting Clothing For a First Date - Tapered Menswear

Planning your outfit for a first date? Remember, it's key to 'dress to impress', especially for men. Here at Tapered Menswear we're known for the perfect fit.

The importance of a well-fitted dress shirt is paramount. A perfectly fitting shirt not only enhances your appearance but also instills a sense of self-confidence. 

With the introduction of TAPERED fit shirts, men now have the option for shirts that are fitted, but have enough stretch to provide comfort for all day wear in comparison to slim fit. A perfect fit for a V taper physique.

Click Here to Shop Better Fitting Dress Shirts

So why not show off all that hard work in the gym with a perfect muscle fit shirt, and be comfortable as well as fashionable?

Check out our best seller here. 

Our Tapered collection also includes muscle fit denim shirtsmuscle fit t-shirts and muscle fit polos.

Our revolutionary cut provides a 10" drop from chest to waist.
Fully fitted in chest and shoulders whilst tapering sharply down, giving a tailored look. No more bagginess in the waist.



Enhanced Darts

Expertly tailored darts at the back, for the perfect fit.


Stretch Cotton

Super soft, breathable and allows complete freedom of movement.



Click Here to Shop Better Fitting Shirts

Perfect for the office. 
With our non obtrusive logo stitched subtly on the wrist makes our Tapered fit Shirt ideal for formal occasions.